Substituted phenyluracils and their use as herbicides

ABSTRACT

Novel substituted phenyluracils of the general formula (I)                    
     in which 
     n represents 0, 1 or 2, 
     R 1  represents hydrogen, amino or optionally substituted alkyl, 
     R 2  represents carboxyl, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted alkyl or alkoxycarbonyl, 
     X represents hydroxyl, mercapto, amino, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, phenylcarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, alkenyl, alkenyloxy, alkenyloxycarbonyl, alkinyl, alkinyloxy or alkinyloxycarbonyl, where in the case that n is greater than 1, X in the individual possible compounds may also have meanings other than those given.

The present invention is the national stage of PCT/EP00/10768 filed Oct.31, 2000, which in turn claims priority of German Patent DE 199 54 312.7filed Nov. 11, 1999.

The invention relates to novel substituted phenyluracils and novelintermediates for their preparation and to their use as herbicides.

Certain substituted aryluracils are already known from the (patent)literature (cf. EP-A-255047, EP-A-260621, EP-A-408382, EP-A-438209,EP-A-473551, EP-A-517181, EP-A-563384, WO-A-91/00278, WO-A-91/07393,WO-A-93/14073, WO-A-98/41093, U.S. Pat. No. 4,979,982, U.S. Pat. No.5,084,084, U.S. Pat. No. 5,127,935, U.S. Pat. No. 5,154,755, U.S. Pat.No. 5,169,430, U.S. Pat. No. 5,486,610, U.S. Pat. No. 5,356,863).However, these compounds have hitherto not attained any particularimportance.

This invention, accordingly, provides novel substituted phenyluracils ofthe general formula (I)

in which

n represents the numbers 0, 1 or 2,

R¹ represents hydrogen, amino or optionally substituted alkyl,

R² represents carboxyl, cyano, carbamoyl, thiocarbamoyl or in each caseoptionally substituted alkyl or alkoxycarbonyl,

X represents hydroxyl, mercapto, amino, nitro, cyano, carboxyl,carbamoyl, thiocarbamoyl, halogen, or represents in each case optionallysubstituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl,alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl,alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyloxy,alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy,phenylcarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino,alkylsulphonylamino, alkenyl, alkenyloxy, alkenyloxycarbonyl, alkinyl,alkinyloxy or alkinyloxycarbonyl—where in the case that n is greaterthan 1, X in the individual possible compounds may also have meaningsother than those given.

In the definitions, the hydrocarbon chains, such as alkyl, are in eachcase straight-chain or branched—including in combination withheteroatoms, such as in alkoxy.

If the compounds of the general formula (I) according to the inventioncontain substituents with asymmetric carbon atoms, the invention relatesin each case to the R enantiomers and the S enantiomers, and to anymixtures of these enantiomers, in particular the racemates.

n preferably represents the numbers 1 or 2.

R¹ preferably represents hydrogen, amino or optionally cyano-,carboxyl-, fluorine-, chlorine-, C₁-C₄-alkoxy- orC₁-C₄-alkoxy-carbonyl-substituted C₁-C₄-alkyl.

R² preferably represents carboxyl, cyano, carbamoyl, thiocarbamoyl or ineach case optionally fluorine-substituted C₁-C₄-alkyl orC₁-C₄-alkoxy-carbonyl.

X preferably represents hydroxyl, mercapto, amino, nitro, cyano,carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine,represents in each case optionally hydroxyl-, cyano-, carboxyl-,carbamoyl-, fluorine-, chlorine-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-,C₁-C₄-alkylsulphinyl-, C₁-C₄-alkylsulphonyl-, C₁-C₄-alkyl-carbonyl-,C₁-C₄-alkoxy-carbonyl-, C₂-C₄-alkenyl-oxycarbonyl-,C₂-C₄-alkinyl-oxycarbonyl-, C₁-C₄-alkylamino-carbonyl-,di-(C₁-C₄-alkyl)-amino-carbonyl-, phenoxycarbonyl-, benzyloxy-carbonyl-,phenylaminocarbonyl-substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl or alkylamino having in each case 1 to 6carbon atoms, represents dialkylamino having in each case 1 to 6 carbonatoms in the alkyl groups, represents in each case optionally cyano-,fluorine-, chlorine-, bromine- or C₁-C₄-alkoxy-substitutedalkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, alkylcarbonyloxy,alkoxycarbonyloxy or alkylaminocarbonyloxy having in each case 1 to 6carbon atoms in the alkyl groups, represents dialkylaminocarbonyl ordialkylaminocarbonyloxy having in each case 1 to 6 carbon atoms in thealkyl groups, represents phenylcarbonyloxy, represents in each caseoptionally fluorine-, chlorine- or bromine-substitutedalkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino having ineach case up to 6 carbon atoms, or represents in each case optionallycyano-, carboxyl-, fluorine-, chlorine-, bromine- orC₁-C₄-alkoxy-carbonyl-substituted alkenyl, alkenyloxy,alkenyloxycarbonyl, alkinyl, alkinyloxy or alkinyloxycarbonyl having ineach case up to 6 carbon atoms.

n particularly preferably represents the number 1.

R¹ particularly preferably represents hydrogen, amino or methyl.

R² particularly preferably represents carboxyl, cyano, carbamoyl,methoxycarbonyl or trifluoromethyl.

X particularly preferably represents hydroxyl, mercapto, amino, nitro,cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine,methyl, represents in each case optionally cyano-, carboxyl-,carbamoyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-,methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-,ethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, acetyl-, propionyl-,n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- ori-propoxycarbonyl-, allyloxycarbonyl-, 1-buten-3-yloxycarbonyl-,2-buten-4-yl-oxycarbonyl-, propargyloxycarbonyl-,1-butin-3-yloxycarbonyl-, 2-butin-4-yloxycarbonyl-,methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-,dimethylaminocarbonyl-, diethylaminocarbonyl-, phenoxycarbonyl-,benzyloxycarbonyl-, phenylaminocarbonyl- orbenzylaminocarbonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-,s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy,methylthio, ethylthio, n- or i-propylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino,ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, representsdimethylamino or diethylamino, represents in each case optionallycyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- ori-propoxy-substituted acetyl, propionyl, n- or i-butyroyl,methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl,acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy,ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy,ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, n- ori-butylaminocarbonyloxy, represents dimethylaminocarbonyl,diethylaminocarbonyl, dimethylaminocarbonyloxy ordiethylaminocarbonyloxy, represents n- or i-butylcarbonyloxy, representsphenylcarbonyloxy, represents in each case optionally fluorine- orchlorine-substituted acetylamino, propionylamino, n- or i-butyroylamino,methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino,methylsulphonylamino, ethylsulphonylamino, n- or i-propylsulphonylamino,n-, i-, s- or t-butylsulphonylamino, or represents in each caseoptionally cyano-, carboxyl-, fluorine-, chlorine-, methoxycarbonyl- orethoxycarbonyl-substituted ethenyl, propenyl, propenyloxy,propenyloxycarbonyl, ethinyl, propinyl, propinyloxy orpropinyloxycarbonyl.

X very particularly preferably represents hydroxyl, mercapto, amino,represents in each case cyano-, carboxyl-, carbamoyl-, chlorine-,methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- ori-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-,ethylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-,methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, n-, i-, s-or t-butoxycarbonyl-, allyloxycarbonyl-, 1-buten-3-yloxycarbonyl-,2-buten-4-yloxycarbonyl-, propargyloxycarbonyl-,1-butin-3-yloxycarbonyl-, 2-butin-4-yloxycarbonyl-,methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-,dimethylaminocarbonyl-, diethylaminocarbonyl-, phenoxycarbonyl-,benzyloxycarbonyl-, phenylaminocarbonyl- orbenzylaminocarbonyl-substituted methyl, methoxy, ethyl, n- or i-propyl,n-, i-, s- or t-butyl, ethoxy, n- or i-propoxy, methylthio, ethylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl,represents in each case cyano-, carboxyl-, carbamoyl-, fluorine-,chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-,n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-,methylsulphonyl-, ethylsulphonyl-, acetyl-, propionyl-, n- ori-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- ori-propoxycarbonyl-, allyloxycarbonyl-, 1-buten-3-yloxycarbonyl-,2-buten-4-yl-oxycarbonyl-, propargyloxycarbonyl-,1-butin-3-yloxycarbonyl-, 2-butin-4-yloxycarbonyl-,methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-,dimethylaminocarbonyl-, diethylaminocarbonyl-, phenoxycarbonyl-,benzyloxycarbonyl-, phenylaminocarbonyl- orbenzylaminocarbonyl-substituted n-, i-, s- or t-butoxy, n- ori-propylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s-or t-butylamino, represents dimethylamino or diethylamino, represents ineach case cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- ori-propoxy-substituted methoxycarbonyl or ethoxycarbonyl, represents ineach case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n-or i-propoxy-substituted acetyl, propionyl, n- or i-butyroyl, n- ori-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- ori-propylaminocarbonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy,methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy,methylaminocarbonyloxy, ethylaminocarbonyloxy, n- ori-propylaminocarbonyloxy, n- or i-butylaminocarbonyloxy, representsdimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminocarbonyloxy ordiethylaminocarbonyloxy, represents n- or i-butylcarbonyloxy, representsphenylcarbonyloxy, represents in each case optionally fluorine- orchlorine-substituted acetylamino, propionylamino, n- or i-butyroylamino,methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino,methylsulphonylamino, ethylsulphonylamino, n- or i-propylsulphonylamino,n-, i-, s- or t-butylsulphonylamino, or represents in each caseoptionally cyano-, carboxyl-, fluorine-, chlorine-, methoxycarbonyl- orethoxycarbonyl-substituted ethenyl, propenyl, propenyloxy,propenyloxycarbonyl, ethinyl, propinyl, propinyloxy orpropinyloxycarbonyl.

X most preferably represents in each case cyano-, carboxyl-, carbamoyl-,methoxy-, ethoxy-, n- or i-propoxy-, methoxycarbonyl-, ethoxycarbonyl-,n- or i-propoxycarbonyl-, allyloxycarbonyl-, 1-buten-3-yloxycarbonyl-,2-buten-4-yloxycarbonyl-, propargyloxycarbonyl-,1-butin-3-yloxycarbonyl-, 2-butin-4-yloxycarbonyl-,methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-,dimethylaminocarbonyl-, diethylaminocarbonyl-, phenoxycarbonyl-,benzyloxycarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl- (andoptionally additionally fluorine- or chlorine-) substituted methyl,ethyl, n-propyl, n-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- ors-butoxy, represents acetyloxy, propionyloxy, n- or i-butyroyloxy,methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy,methylaminocarbonyloxy, ethylaminocarbonyloxy, n- ori-propylaminocarbonyloxy, dimethylaminocarbonyloxy,diethylaminocarbonyloxy or phenylcarbonyloxy, represents n- ori-butylcarbonyloxy, represents dimethylamino, n- ori-butylaminocarbonyloxy, or represents in each case cyano-, carboxyl-,methoxycarbonyl- or ethoxycarbonyl- (and optionally additionallyfluorine- or chlorine-) substituted ethenyl, propenyl, propenyloxy,ethinyl, propinyl or propinyloxy.

Preference according to the invention is given to the compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred.

Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

Very particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being very particularly preferred.

Most preference according to the invention is given to the compounds ofthe formula (I) which contain a combination of the meanings listed aboveas being most preferred.

A very particularly preferred group are the compounds of the formula (I)

in which

n represents 1 or 2,

R¹ represents hydrogen or methyl,

R² represents trifluoromethyl, carbamoyl, carboxyl, methoxycarbonyl orcyano, and

X represents hydroxyl, mercapto, amino, nitro, cyano, carboxyl,carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or represents ineach case optionally cyano-, carboxyl-, carbamoyl-, fluorine-,chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methoxycarbonyl-,ethoxycarbonyl-, n- or i-propoxycarbonyl-, allyloxycarbonyl-,propargyloxycarbonyl-, 1-buten-3-yloxycarbonyl-,2-buten-4-yloxycarbonyl-, propargyloxycarbonyl-,1-butin-3-yloxycarbonyl-, 2-butin-4-yloxycarbonyl-,methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-,dimethylaminocarbonyl-, diethylaminocarbonyl-, phenoxycarbonyl-,benzyloxycarbonyl-, phenylaminocarbonyl- orbenzylaminocarbonyl-substituted methyl, ethyl, methoxy, ethoxy,methylthio, ethylthio, methoxycarbonyl or ethoxycarbonyl, or representsmethoxycarbonyl- or ethoxycarbonyl-substituted ethenyl, or

X represents in each case cyano-, carboxyl-, carbamoyl-, methoxy-,ethoxy-, n- or i-propoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- ori-propoxycarbonyl-, allyloxycarbonyl-, 1-buten-3-yl-oxycarbonyl-,2-buten-4-yloxycarbonyl-, propargyloxycarbonyl-,1-butin-3-yloxycarbonyl-, 2-butin-4-yloxycarbonyl-,methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-,dimethylaminocarbonyl-, diethylaminocarbonyl-, phenoxycarbonyl-,benzyloxycarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl- (andoptionally additionally fluorine- or chlorine-) substituted methyl,ethyl, n-propyl, n-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- ors-butoxy, represents acetyloxy, propionyloxy, n- or i-butyroyloxy,methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy,methylaminocarbonyloxy, ethylaminocarbonyloxy, n- ori-propylaminocarbonyloxy, dimethylaminocarbonyloxy,diethylaminocarbonyloxy or phenylcarbonyloxy, represents n- ori-butylcarbonyloxy, represents dimethylamino, n- ori-butylaminocarbonyloxy, or represents in each case cyano-, carboxyl-,methoxycarbonyl- or ethoxycarbonyl- (and optionally additionallyfluorine- or chlorine-) substituted ethenyl, propenyl, propenyloxy,ethinyl, propinyl or propinyloxy.

A further very particularly preferred group are those compounds of theformula (I) in which

n represents 1 or 2,

R¹ represents methyl,

R² represents trifluoromethyl, carbamoyl, carboxyl, cyano ormethoxycarbonyl, and

X has one of the meanings given above for compounds of the formula (I).

A further very particularly preferred group are those compounds of theformula (I) in which

n represents 1 or 2,

R¹ represents hydrogen,

R² represents trifluoromethyl, carbamoyl, carboxyl, cyano ormethoxycarbonyl, and

X has one of the meanings given above for compounds of the formula (I).

A further very particularly preferred group are those compounds of theformula (I) in which

n represents 1 or 2,

R¹ represents hydrogen or methyl,

R² represents trifluoromethyl, and

X has one of the meanings given above for compounds of the formula (I).

A further very particularly preferred group are those compounds of theformula (IA)

in which

R¹ represents hydrogen or methyl,

R² represents trifluoromethyl, and

X represents in each case carboxyl-, methoxycarbonyl-, ethoxycarbonyl-,n- or i-propoxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-,dimethylaminocarbonyl-, diethylaminocarbonyl- orphenylaminocarbonyl-substituted methyl, ethyl, methoxy, ethoxy, or

X represents n- or i-butylaminocarbonyloxy, n- or i-butylcarbonyloxy,dimethylamino, methoxycarbonyloxy, ethoxycarbonyloxy,methylaminocarbonyloxy, ethylaminocarbonyloxy, or representsdimethylaminocarbonyloxy.

A further very particularly preferred group are those compounds of theformula (IA) in which

R¹ represents hydrogen or methyl,

R² represents trifluoromethyl, and

X represents in each case carboxyl-, methoxycarbonyl- orethoxycarbonyl-substituted methyl, methoxy or ethoxy, or

X represents methoxycarbonyloxy, ethoxycarbonyloxy,methylaminocarbonyloxy or ethylaminocarbonyloxy.

The abovementioned general or preferred radical definitions apply bothto the end products of the formula (I) and, correspondingly, to thestarting materials or intermediates required in each case for thepreparation. These radical definitions can be combined with one anotherat will, i.e. including combinations between the given preferred ranges.

Examples of the compounds of the general formula (I) according to theinvention are listed in the groups below.

Group 1

X¹ has here the meanings given in the list below:

4-(1-carboxy)-ethoxy, 4-(1-ethoxycarbonyl)-ethoxy,3-(1-ethoxycarbonyl)-ethoxy, 3-ethoxycarbonylmethoxy,2-(1-ethoxycarbonyl)-ethoxy.

Group 2

X¹ represents dimethylaminocarbonylmethoxy or methylaminocarbonylmethoxyand

X² represents methyl.

Group 3

X¹ represents phenylaminocarbonylethoxy or phenylaminocarbonylmethoxy.

Group 4

X¹ represents n- or i-butylcarbonyloxy or ethoxycarbonyloxy.

Group 5

X¹ represents 4-ethylaminocarbonyloxy, 4-(n- ori-)butylaminocarbonyloxy, 3-methylaminocarbonyloxy or2-methylaminocarbonyloxy.

Group 6

X¹ represents dimethylamino and

R¹ represents hydrogen or methyl.

Group 7

X¹ represents 2-chloro, 3-chloro, 4-chloro, 3-fluoro, 4-fluoro,3-methyl, 3-cyano, 4-cyano, 2-methylthio, 2-methylsulphinyl or4-methylsulphinyl.

Group 8

X¹ represents 2-chloro, 3-chloro, 4-chloro, 2-fluoro, 4-fluoro,3-methyl, 3-nitro, 4-methyl, 3-cyano, 4-cyano, 2-methylthio, 4-nitro,2-cyano, 4-methylthio or 2-methoxy.

Group 9

X_(n) represents (3,4-)Cl₂ or (2,4-)F₂.

Group 10

X_(n) represents (3,4-)Cl₂ or (2,4-)F₂.

Group 11

X¹ represents hydroxyl or methoxy, and

X² represents methyl.

Group 12

X¹ represents 4-methoxy, 3-chloro or 4-cyano.

Group 13

X¹ represents 3-trifluoromethyl, 4-chloro, 3-methoxy, 3-chloro or4-cyano.

Group 14

X¹ represents 3-methoxy, 3-chloro or 4-cyano.

Group 15

X¹ represents 3-trifluoromethyl, 4-chloro, 3-methoxy, 3-chloro or4-cyano.

Group 16

R² represents methoxycarbonyl, carbamoyl or cyano.

Group 17

R² represents carbamoyl or cyano.

The novel substituted phenyluracils of the general formula (I) haveinteresting biological properties. In particular, they have strongherbicidal activity.

The novel substituted phenyluracils of the general formula (I) areobtained when

(a) halogenophenyluracils of the general formula (II)

 in which

R¹ and R² are each as defined above and

X³ represents halogen,

are reacted with aryl compounds of the general formula (III)

 in which

n and X are each as defined above,

or with metal salts of compounds of the general formula (III),

if appropriate in the presence of a reaction auxiliary and ifappropriate in the presence of a diluent,

or when

(b) aminoalkenoic esters of the general formula (I)

 in which

R² is as defined above and

R represents alkyl, aryl or arylalkyl,

are reacted with aryl isocyanates of the general formula (V)

 in which

n and X are each as defined above,

or with arylurethanes (arylcarbamates) of the general formula (VI)

 in which

n and X are each as defined above and

R represents alkyl, aryl or arylalkyl,

if appropriate in the presence of a reaction auxiliary and ifappropriate in the presence of a diluent,

or when

(c) N-aryl-1-alkoxycarbonylamino-maleimides of the general formula (VII)

 in which

n and X are each as defined above and

R′ represents alkyl,

are reacted with a metal hydroxide in the presence of water and, ifappropriate, in the presence of an organic solvent,

or when

(d) substituted phenyluracils of the general formula (Ia)

 in which

n and X are each as defined above

are reacted with 1-aminooxy-2,4-dinitro-benzene or with alkylatingagents of the general formula (VIII)

X⁴—A¹ (VIII)

 in which

A¹ represents optionally substituted alkyl and

X⁴ represents halogen or the grouping —O—SO₂—O—A¹,

if appropriate in the presence of a reaction auxiliary and ifappropriate in the presence of a diluent, and electrophilic ornucleophilic and/or oxidation or reduction reactions within the scope ofthe definition of the substituents are, if appropriate, subsequentlycarried out in a customary manner.

The compounds of the general formula (I) can be converted by customarymethods into other compounds of the general formula (I) according to theabove definition, for example by esterification or hydrolysis (forexample X: OCH₂COOH→OCH₂COOC₂H₅, OCH(CH₃)COOCH₃→OCH(CH₃)COOH),conversion of carboxyl compounds into other carboxylic acid derivativesby customary methods (for example R²: COOH→CN, CN→CSNH₂, COOH→COOCH₃,COOCH₃→CONH₂); cf. the Preparation Examples).

Using, for example,1-(4-cyano-2,5-difluoro-phenyl)-4-chlorodifluoromethyl-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidineand ethyl 1(4-hydroxy-phenoxy)-propionate as starting materials, thecourse of the reaction in the process (a) according to the invention canbe illustrated by the following reaction scheme:

Using, for example, methyl 3-amino-4,4,4-trifluoro-crotonate and4-cyano-2-fluoro-5-phenoxy-phenyl isocyanate as starting materials, thecourse of the reaction in process (b) according to the invention can beillustrated by the following reaction scheme:

Using, for example, methyl[1-(4-cyano-2-fluoro-5-phenoxy-phenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-carbamateas starting material, the course of the reaction in the process (c)according to the invention can be illustrated by the following reactionscheme:

Using, for example,1-[2-fluoro-4-cyano-5-(4-methoxycarbonylmethoxy-phenoxy)-phenyl]-4-difluoromethyl-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidineand methyl bromide as starting materials, the course of the reaction inthe process (d) according to the invention can be illustrated by thefollowing reaction scheme:

The formula (II) provides a general definition of thehalogenophenyluracils to be used as starting materials in the process(a) according to the invention for preparing compounds of the formula(I). In the formula (II), R¹ and R² each in particular have thosemeanings which have already been mentioned above, in connection with thedescription of the compounds of the formula (I) according to theinvention, as being preferred, particularly preferred or veryparticularly preferred for R¹ and R²; X³ preferably represents fluorineor chlorine, in particular fluorine.

The starting materials of the general formula (II) are known and/or canbe prepared by processes known per se (cf. EP-A-648749).

The formula (III) provides a general definition of the aryl compoundsfurther to be used as starting materials in the process (a) according tothe invention. In the formula (III), n and X each in particular havethose meanings which have already been mentioned above, in connectionwith the description of the compounds of the formula (I) according tothe invention, as being preferred, particularly preferred or veryparticularly preferred for n and X.

The starting materials of the general formula (III) are known organicchemicals for synthesis.

The formula (IV) provides a general definition of the aminoalkenoicesters to be used as starting materials in the process (b) according tothe invention for preparing compounds of the general formula (I). In thegeneral formula (IV), R² in particular has that meaning which hasalready been mentioned above, in connection with the description of thecompounds of the general formula (I) according to the invention, asbeing preferred, particularly preferred or very particularly preferredfor R²; R preferably represents C₁-C₄-alkyl, phenyl or benzyl, inparticular methyl or ethyl.

The starting materials of the general formula (IV) are known and/or canbe prepared by processes known per se (cf. J. Heterocycl. Chem. 9(1972), 513-522).

The formula (V) provides a general definition of the aryl isocyanatesfurther to be used as starting materials in the process (b) according tothe invention. In the general formula (V), n and X each in particularhave those meanings which have already been mentioned above, inconnection with the description of the compounds of the general formula(I) according to the invention, as being preferred, particularlypreferred or very particularly preferred for n and X.

The novel aryl isocyanates of the general formula (V) are obtained whenaniline derivatives of the general formula (IX)

in which

n and X are each as defined above,

are reacted with phosgene in the presence of a diluent, such as, forexample, chlorobenzene, at temperatures between −20° C. and +150° C.(cf., for example, also EP-A-648749).

The formula (VI) provides a general definition of the arylurethanes tobe used, if appropriate, as starting materials in the process (b)according to the invention. In the general formula (VI), n and X each inparticular have those meanings which have already been mentioned above,in connection with the description of the compounds of the generalformula (I) according to the invention, as being preferred, particularlypreferred or very particularly preferred for n and X; R preferablyrepresents C₁-C₄-alkyl, phenyl or benzyl, in particular methyl or ethyl.

The novel arylurethanes of the general formula (VI) are obtained whenaniline derivatives of the general formula (IX)

in which

n and X are each as defined above,

are reacted with chlorocarbonyl compounds of the general formula (X)

RO—CO—Cl  (X)

 in which

R is as defined above,

if appropriate in the presence of an acid acceptor, such as, forexample, pyridine, and if appropriate in the presence of a diluent, suchas, for example, methylene chloride, at temperatures between −20° C. and+100° C. (cf. the Preparation Examples).

The aniline derivatives of the general formula (IX) required asprecursors have hitherto not been disclosed.

The aniline derivatives of the general formula (IX)

 in which

n and X are each as defined above,

are obtained when anilines of the general formula (XI)

 in which

X³ is as defined above,

are reacted with phenols of the general formula (III)

 in which

n and X are each as defined above,

or with metal salts of compounds of the general formula (III),

if appropriate in the presence of a reaction auxiliary, such as, forexample, sodium hydride, and if appropriate in the presence of adiluent, such as, for example, N-methylpyrrolidone, at temperaturesbetween 0° C. and 150° C. (cf. the Preparation Examples).

The formula (VII) provides a general definition of theN-aryl-1-alkoxycarbonyl-amino-maleimides to be used as startingmaterials in the process (c) according to the invention for preparingcompounds of the general formula (I). In the general formula (VII), nand X each in particular have those meanings which have already beenmentioned above, in connection with the description of the compounds ofthe general formula (I) according to the invention, as being preferred,particularly preferred or very particularly preferred for n and X; R′preferably represents C₁-C₄-alkyl, in particular methyl or ethyl.

The N-aryl-1-alkoxycarbonylamino-maleimides of the general formula (VII)are obtained when alkyl (2,5-dioxo-2,5-dihydro-furan-3-yl)-carbamates ofthe general formula (XII)

in which

R′ represents alkyl (in particular methyl or ethyl),

are reacted with aniline derivatives of the general formula (IX)

 in which

n and X are each as defined above,

if appropriate in the presence of a diluent such as, for example, aceticacid, at temperatures between 0° C. and 200° C., preferably between 50°C. and 150° C.

The precursors of the general formula (XII) are known and/or can beprepared by processes known per se (cf. DE 19604229).

The formula (Ia) provides a general definition of the substitutedphenyluracils to be used as starting materials in the process (d)according to the invention for preparing compounds of the formula (I).In the formula (Ia), n and X each in particular have those meaningswhich have already been mentioned above, in connection with thedescription of the compounds of the formula (I) according to theinvention, as being preferred, particularly preferred or veryparticularly preferred for n and X.

The starting materials of the general formula (Ia) for process (d) canbe prepared by the processses (a), (b) and (c) according to theinvention.

The formula (VIII) provides a general definition of the alkylatingagents further to be used as starting materials in the process (d)according to the invention. In the formula (VIII), A¹ preferablyrepresents optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkylhaving 1 to 4 carbon atoms and X² represents chlorine, bromine, iodine,methylsulphonyloxy or ethylsulphonyloxy: in particular, A¹ represents ineach case optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl and X² representschlorine, bromine, iodine, methylsulphonyloxy or ethylsulphonyloxy.

The starting materials of the formula (VIII) are known organic chemicalsfor synthesis.

The processes according to the invention for preparing the compounds ofthe general formula (I) are preferably carried out using diluents.Suitable diluents for carrying out the processes (a), (b), (c) and (d)according to the invention are, in addition to water, especially inertorganic solvents. These include, in particular, aliphatic, alicyclic oraromatic, optionally halogenated hydrocarbons, such as, for example,benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene,petroleum ether, hexane, cyclohexane, dichloromethane, chloroform,carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether,dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethyleneglycol diethyl ether; ketones, such as acetone, butanone or methylisobutyl ketone; nitriles, such as acetonitrile, propionitrile orbutyronitrile; amides, such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone orhexamethylphosphoric triamide; esters, such as methyl acetate or ethylacetate, sulphoxides, such as dimethyl sulphoxide, alcohols, such asmethanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether,ethylene glycol monoethyl ether, diethylene glycol monomethyl ether,diethylene glycol monoethyl ether, mixtures thereof with water or purewater.

Suitable reaction auxiliaries for the processes (a), (b), (c) and (d)according to the invention are, in general, the customary inorganic ororganic bases or acid acceptors. These preferably include alkali metalor alkaline earth metal acetates, amides, carbonates, bicarbonates,hydrides, hydroxides or alkoxides, such as, for example, sodium acetate,potassium acetate or calcium acetate, lithium amide, sodium amide,potassium amide or calcium amide, sodium carbonate, potassium carbonateor calcium carbonate, sodium bicarbonate, potassium bicarbonate orcalcium bicarbonate, lithium hydride, sodium hydride, potassium hydrideor calcium hydride, lithium hydroxide, sodium hydroxide, potassiumhydroxide or calcium hydroxide, sodium methoxide, ethoxide, n- ori-propoxide, n-, i-, s- or t-butoxide, or potassium methoxide, ethoxide,n- or i-propoxide, n-, i-, s- or butoxide; furthermore also basicorganic nitrogen compounds, such as, for example, trimethylamine,triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine,N,N-dimethyl-cyclohexylamine, dicyclohexylamine,ethyl-dicyclohexylamine, N,N-dimethyl-aniline, N,N-dimethyl-benzylamine,pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-,3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine,4-dimethylamino-pyridine, N-methyl-piperidine,1,4-diazabicyclo[2.2.2]-octane, (DABCO),1,5-diazabicyclo[4.3.0]-non-5-ene (DBN) or1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU).

Suitable further reaction auxiliaries for the processses according tothe invention are also phase-transfer catalysts. Examples of suchcatalysts which may be mentioned are:

Tetrabutylammonium bromide, tetrabutylammonium chloride,tetraoctylammonium chloride, tetrabutylammonium hydrogen sulphate,methyl-trioctylammonium chloride, hexadecyl-trimethylammonium chloride,hexadecyl-trimethylammonium bromide, benzyl-trimethylammonium chloride,benzyl-triethylammonium chloride, benzyl-trimethylammonium hydroxide,benzyl-triethylammonium hydroxide, benzyl-tributylammonium chloride,benzyl-tributylammonium bromide, tetrabutylphosphonium bromide,tetrabutylphosphonium chloride, tributyl-hexadecylphosphonium bromide,butyl-triphenylphosphonium chloride, ethyl-trioctylphosphonium bromide,tetraphenylphosphonium bromide.

When carrying out the processes (a), (b), (c) and (d) according to theinvention the reaction temperatures can be varied within a relativelywide range. In general, the processes are carried out at temperaturesbetween 0° C. and 150° C., preferably between 10° C. and 120° C.

The processes according to the invention are generally carried out underatmospheric pressure. However, it is also possible to carry out theprocesses according to the invention under elevated or reducedpressure—in general between 0.1 bar and 10 bar.

For carrying out the processes according to the invention, the startingmaterials are generally employed in approximately equimolar amounts.However, it is also possible to use a relatively large excess of one ofthe components. The reaction is generally carried out in a suitablediluent in the presence of a reaction auxiliary, and the reactionmixture is generally stirred at the required temperature for severalhours. Work-up is carried out by customary methods (cf. the PreparationExamples).

The active compounds according to the invention can be used asdefoliants, desiccants, haulm killers and, especially, as weed killers.By weeds in the broadest sense there are to be understood all plantswhich grow in locations where they are undesired. Whether the substancesaccording to the invention act as total or selective herbicides dependsessentially on the amount used. The active compounds according to theinvention can be used, for example, in connection with the followingplants:

Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium,Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica,Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea,Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum,Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura,Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.

Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus,Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.

Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis,Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrostis, Alopecurus, Apera.

Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum,Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants. Depending on the concentration, the compoundsare suitable for total weed control, for example on industrial terrainand rail tracks and on paths and areas with and without tree growth.Equally, the compounds can be employed for controlling weeds inperennial crops, for example forests, ornamental tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hop fields, onlawns and turf and pastures and for selective weed control in annualcrops.

The compounds of the formula (I) according to the invention have strongherbicidal activity and a broad activity spectrum when used on the soiland above-ground parts of plants. To a certain extent, they are alsosuitable for selective control of monocotyledonous and dicotyledonousweeds in monocotyledonous and dicotyledonous crops, both by thepre-emergence and by the post-emergence method.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspo-emulsion concentrates,natural and synthetic substances impregnated with active compound, andmicroencapsulations in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is to say liquid solventsand/or solid carriers, optionally with the use of surfactants, that isto say emulsifiers and/or dispersants and/or foam formers.

If the extender used is water, it is also possible to use, for example,organic solvents as auxiliary solvents. Liquid solvents which are mainlysuitable are: aromatics, such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics and chlorinated aliphatic hydrocarbons, such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons, such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols, such as butanol orglycol, and also their ethers and esters, ketones, such as acetone,methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, stronglypolar solvents, such as dimethylformamide and dimethyl sulphoxide, andwater.

Suitable solid carriers are: for example ammonium salts and groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as finely divided silica, alumina and silicates; suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks, such as calcite, marble, pumice, sepiolite, dolomite andsynthetic granules of inorganic and organic meals, and granules oforganic material, such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifiers and/or foam formers are: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand protein hydrolysates; suitable dispersants are: for examplelignosulphite waste liquors and methylcellulose.

Tackifiers, such as carboxymethylcellulose, natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, and also naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants, such as inorganic pigments, for exampleiron oxide, titanium oxide, Prussian blue, and organic dyestuffs, suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients, such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 percent by weightof active compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention,as such or in the form of their formulations, can also be used asmixtures with known herbicides, finished formulations or tank mixesbeing possible.

Possible components for the mixtures are known herbicides, for exampleacetochlor, acifluorfen(-sodium), aclonifen, alachlor,alloxydim(-sodium), ametryne, amidochlor, amidosulfuron, anilofos,asulam, atrazine, azafenidin, azimsulfuron, benazolin(-ethyl),benfuresate, bensulfuron(-methyl), bentazon, benzofenap,benzoylprop(-ethyl), bialaphos, bifenox, bispyribac(-sodium),bromobutide, bromofenoxim, bromoxynil, butachlor, butroxydim, butylate,cafenstrole, caloxydim, carbetamide, carfentrazone(-ethyl),chlomethoxyfen, chloramben, chloridazon, chlorimuron(-ethyl),chlornitrofen, chlorsulfuron, chlortoluron, cinidon(-ethyl),cinmethylin, cinosulfuron, clethodim, clodinafop(-propargyl), clomazone,clomeprop, clopyralid, clopyrasulfuron(-methyl), cloransulam(-methyl),cumyluron, cyanazine, cybutryne, cycloate, cyclosulfamuron, cycloxydim,cyhalofop(-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate,dicamba, diclofop(-methyl), diclosulam, diethatyl(-ethyl), difenzoquat,diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethacblor,dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid,diquat, dithiopyr, diuron, dymron, epoprodan, EPTC, esprocarb,ethalfluralin, ethametsulfuron(-methyl), ethoflimesate, ethoxyfen,ethoxysulfuron, etobenzanid, fenoxaprop(-P-ethyl), flamprop(-isopropyl),flamprop(-isopropyl-L), flamprop(-methyl), flazasulfuron,fluazifop(-P-butyl), fluazolate, flucarbazone, flufenacet, flumetsulam,flumiclorac(-pentyl), flumioxazin, flumipropyn, flumetsulam,fluometuron, fluorochloridone, fluoroglycofen(-ethyl), flupoxam,flupropacil, flurpyrsulfuron(-methyl, -sodium), flurenol(-butyl),fluridone, fluroxypyr(-meptyl), flurprimidol, flurtamone,fluthiacet(-methyl), fluthiamide, fomesafen, glufosinate(-ammonium),glyphosate(-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl),haloxyfop(-P-methyl), hexazinone, imazamethabenz-(-methyl),imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr,imazosuIlfumn, iodosulfuron, ioxynil, isopropalin, isoproturon, isouron,isoxaben, isoxachlorbole, isoxaflutole, isoxapyrifop, lactofen, lenacil,linuron, MCPA, MCPP, mefenacet, mesotrione, metamitron, metazachlor,methabenzthiazuron, metobenzuron, metobromuron, (alpha-)metolachlor,metosulam, metoxuron, metribuzin, metsulfuron(-methyl), molinate,monolinuron, naproanilide, napropamide, neburon, nicosulfuron,norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasuilfron,oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin,pentoxazone, phenmedipham, piperophos, pretilachlor,primisulfuron(-methyl), prometryn, propachlor, propanil, propaquizafop,propisochlor, propyzamide, prosulfocarb, prosulfuron,pyraflufen(-ethyl), pyrazolate, pyrazosulfuron(-ethyl), pyrazoxyfen,pyribenzoxim, pyributicarb, pyridate, pyriminobac(-methyl),pyrithiobac(-sodium), quinchlorac, quimnerac, quinoclamine,quizalofop(-P-ethyl), quizalofop(-P-tefuryl), rimsulfuron, sethoxydim,simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl),sulfosate, sulfosulfuiron, tebutam, tebuthiuron, tepraloxydim,terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr,thidiazimin, thifensulfuron(-methyl), thiobencarb, tiocarbazil,tralkoxydim, triallate, triasulfuron, tribenuron(-methyl), triclopyr,tridiphane, trifluralin and triflusulfuron.

A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomizing, scattering.

The active compounds according to the invention can be applied bothbefore and after emergence of the plants. They can also be incorporatedinto the soil before sowing.

The amount of active compound used can vary within a relatively widerange. It depends essentially on the nature of the desired effect. Ingeneral, the amounts used are between 1 g and 10 kg of active compoundper hectare of soil surface, preferably between 5 g and 5 kg per ha.

The preparation and the use of the active compounds according to theinvention can be seen from the examples below.

PREPARATION EXAMPLES Example 1

(Process (a))

2.5 g (10 mmol) of 4-methoxy-phenol are initially charged in 50 ml ofdimethyl sulphoxide and admixed with 1.6 g of sodium hydride (60% pure).The mixture is stirred at room temperature (approximately 20° C.) for 30minutes. 3.2 g (10 mmol) of4-(3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidin-1-yl)-2,5-difluoro-benzonitrileare then added. The reaction mixture is stirred at 60° C. for 18 hoursand then poured into about the same amount by volume of 1N hydrochloricacid. The resulting crystalline product is isolated by filtration withsuction, stirred with a mixture of 30 ml of ethyl acetate and 300 ml ofdiethyl ether and filtered off with suction until dry. The organicmother liquor is concentrated under waterpump vacuum and the residue isworked up by column chromatography (silica gel, chloroform/ethylacetate, vol.: 2:1). The resulting first fraction is concentrated underwaterpump vacuum, the residue is dissolved in boiling methylenechloride, the supernatant solvent is decanted off after cooling, theresidue is stirred with diethyl ether/diisopropyl ether and thecrystalline product is isolated by filtration with suction.

This gives 0.90 g (21% of theory) of4-(3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidin-1-yl)-5-fluoro-2-(4-methoxy-phenoxy)-benzonitrileof melting point 84° C.

Example 2

(Process (b))

A mixture of 0.50 g (1.2 mmol) of4-(3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidin-1-yl)-5-fluoro-2-(4-methoxy-phenoxy)-benzonitrile,0.20 g (1.8 mmol) of dimethyl sulphate, 0.30 g (2.4 mmol) of potassiumcarbonate and 100 ml of acetone is heated under reflux for 15 hours andthen concentrated under waterpump vacuum. The residue is shaken with 50ml of 1N hydrochloric acid/50 ml of ethyl acetate and the organic phaseis separated off, dried with sodium sulphate and filtered. The filtrateis concentrated under waterpump vacuum, dissolved in ethyl acetate,washed with 5% strength aqueous disodium hydrogen phosphate solution,dried with sodium sulphate and filtered. The filtrate is concentratedunder waterpump vacuum, the residue is stirred with petroleum ether andthe solvent is carefully distilled off under waterpump vacuum.

This gives 0.3 g (57% of theory) of4-(3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoro-methyl-1(2H)-pyrimidin-1-yl)-5-fluoro-2-(4-methoxy-phenoxy)-benzonitrileof melting point 62° C.

Analogously to Preparation Examples 1 and 2, and in accordance with thegeneral description of the preparation processes according to theinvention, it is also possible to prepare, for example, the compounds ofthe formula (I) listed in Table 1 below.

TABLE 1 Examples of the compounds of the formula (I) Physical data Ex.and stereochem. No. N Q R¹ R² R³ R⁴ R⁵ (position-) X specifications 3 1O CH₃ CF₃ H F CN (4-) racemate

m.p.: 155° C. 4 1 O CH₃ CF₃ H F CN (4-) racemate

m.p.: 140° C. 5 1 O CH₃ CF₃ H F CN (4-)

6 1 O CH₃ CF₃ H F CN (4-) m.p.: 90° C.

7 1 O CH₃ CF₃ H F CN (4-) m.p.: 110° C.

8 1 O CH₃ CF₃ H F CN (4-)

9 1 O CH₃ CF₃ H F CN (4-) (R isomer

R/S = >9:<1) 10 1 O CH₃ CF₃ H F CN (4-) m.p.: 152° C.

δ = 6.55 ppm (s, D₆-DMSO) 11 0 O H CF₃ H F CN — m.p.: 223° C. 12 0 O NH₂CF₃ H F CN — 13 1 O CH₃ CF₃ H F CN (2-)Cl m.p.: 206° C. 14 1 O H CF₃ H FCN (3-)Cl m.p.: 86° C. 15 1 O CH₃ CF₃ H F CN (3-)Cl m.p.: 101° C. 16 1 OH CF₃ H F CN (4-)Cl m.p.: 196° C. 17 1 O CH₃ CF₃ H F CN (4-)Cl m.p.:150° C. 18 1 O H CF₃ H F CN (2-)F m.p.: 210° C. 19 1 O CH₃ CF₃ H F CN(3-)F m.p.: 78° C. 20 1 O H CF₃ H F CN (4-)F m.p.: 143° C. 21 1 O CH₃CF₃ H F CN (4-)F m.p.: 169° C. 22 2 O H CF₃ H F CN (3,4-)Cl₂ δ = 6.43ppm (s, D₆-DMSO) 23 2 O CH₃ CF₃ H F CN (3,4-)Cl₂ m.p.: 96° C. 24 2 O HCF₃ H F CN (2,4-)F₂ m.p.: 177° C. 25 2 O CH₃ CF₃ H F CN (2,4-)F₂ m.p.:154° C. 26 1 O H CF₃ H F CN (3-)CH₃ m.p.: 139° C. logP = 2.92^(a)) 27 1O CH₃ CF₃ H F CN (3-)CH₃ m.p.: 158° C. logP = 3.52^(a)) 28 1 O H CF₃ H FCN (3-)N(CH₃)₂ m.p.: 192° C. logp = 2.63^(a)) 29 1 O CH₃ CF₃ H F CN (3-)N(CH₃)₂ m.p.: 142° C. logP = 3.36^(a)) 30 1 O H CF₃ H F CN (3-)NO₂ m.p.:183° C. 31 1 O H CF₃ H F CN (4-)CH₃ m.p.: 164° C. 32 1 O H CF₃ H F CN(3-)CN m.p.: 149° C. 33 1 O CH₃ CF₃ H F CN (3-)CN m.p.: 84° C. 34 1 O HCF₃ H F CN (4-)CN m.p.: 143° C. 35 1 O CH₃ CF₃ H F CN (4-)CN m.p.: 110°C. 36 1 O H CF₃ H F CN (2-)SCH₃ logP = 2.78^(a)) δ = 6.36 ppm (s,D₆-DMSO) 37 1 O CH₃ CF₃ H F CN (2-)SCH₃ m.p.: 120° C. logP = 3.36^(a))38 1 O CH₃ CF₃ H F CN (2-)SO₂CH₃ 39 1 O H CF₃ H F CN (2-)Cl 40 1 O H CF₃H F CN (4-)NO₂ 41 1 O H CF₃ H F CN (2-)CN 42 1 O H CF₃ H F CN (4-)SCH₃m.p.: 84° C. logP = 2.95^(a)) 43 1 O CH₃ CF₃ H F CN (4-)SO₂CH₃ 44 1 OCH₃ CF₃ H F CN (3-) R enantiomer

δ = 6.56 ppm (s, D₆-DMSO) 45 1 O CH₃ CF₃ H F CN (3-) δ = 6.56 ppm

(s, D₆-DMSO) 46 1 O CH₃ CF₃ H F CN (3-) δ = 6.56 ppm

(s, D₆-DMSO) 47 1 O H CF₃ H F CN (2-)OCH₃ m.p.: 86° C. 48 1 O CH₃ CF₃ HF CN (2-)

49 1 O CH₃ CF₃ H F CN (2-) m.p.: 108° C.

log P = 2.66^(a)) 50 2 O CH₃ CF₃ H F CN (2-)OCH₃ m.p.: 143° C. (5-)CH₃log P = 3.48^(a)) 51 2 O CH₃ CF₃ H F CN (2-)OH m.p.: 174° C. (5-)CH₃ logP = 2.96^(a)) 52 2 O CH₃ CF₃ H F CN (2-) m.p.: 203° C.

log P = 2.93^(a)) (5-)CH₃ 53 2 O CH₃ CF₃ H F CN (2-) m.p.: 117° C.

log P = 2.91^(a)) (5-)CH₃ 54 2 O CH₃ CF₃ H F CN (2-)

(5-)CH₃ 55 1 O CH₃ CF₃ H F CN (4-) m.p.: 91° C.

56 1 O CH₃ CF₃ H F CN (4-) m.p.: 97° C.

(racemate) 57 1 O H

H F CN (4-)OCH₃ 58 2 O CH₃

H F CN (2-)Cl, (4-)OCH₃ 59 1 O CH₃

H F CN (3-)OCH₃ 60 1 O CH₃

H F CN (3-)CF₃ logP = 2.40^(a)) 61 1 O CH₃

H F CN (4-)Cl logP = 2.20^(a)) 62 2 O CH₃

H F CN (3-)Cl, (4-)Cl logP = 2.51^(a)) 63 2 O CH₃

H F CN (2-)Cl, (4-)OCH3 logP = 2.16^(a)) 64 1 O CH₃

H F CN (3-)OCH₃ logP = 1.98^(a)) 65 1 O CH₃ CN H F CN (3-)CF₃ m.p.: 108°C. logP = 3.21^(a)) 66 1 O CH₃ CN H F CN (4-)Cl m.p.: 198° C. logP =3.04^(a)) 67 1 O H

H F CN (3-)Cl logP = 1.89^(a)) 68 1 O H

H F CN (4-)CN logP = 1.49^(a)) 69 2 O CH₃ CN H F CN (3-)Cl, m.p.: 191°C. (4-)Cl logP = 3.37^(a)) 70 1 O CH₃

H F CN (3-)Cl 71 1 O CH₃

H F CN (4-)CN 72 1 O CH₃

H F CN (3-)Cl logP = 2.19^(a)) 73 1 O CH₃

H F CN (4-)CN logP = 1.75^(a)) 74 2 O CH₃ CN H F CN (2-)Cl, m.p.: 176°C. (4-)OCH3 logP = 2.93^(a)) 75 1 O CH₃ CN H F CN (3-)OCH₃ m.p.: 202° C.logP = 2.75^(a)) 76 1 0 CH₃ CN H F CN (3-)Cl m.p.: 80° C. logP =3.04^(a)) 77 1 O CH₃ CN H F CN (4-)CN m.p.: 232° C. logP = 2.44^(a))

The logP values given in Table 1 were determined in accordance with EECdirective 79/831 Annex V.A8 by HPLC (High Performance LiquidChromatography) using a reverse-phase column (C 18). Temperature: 43° C.

(a) Mobile phases for the determination in the acidic range: 0.1%aqueous phosphoric acid, acetonitrile; linear gradient from 10%acetonitrile to 90% acetonitrile—the corresponding data in Table 1 arelabelled a).

(b) Mobile phases for the determination in the neutral range: 0.01 molaraqueous phosphate buffer solution, acetonitrile; linear gradient from10% acetonitrile to 90% acetonitrile—the corresponding data in Table 1are labelled b).

Calibration was carried out using unbranched alkan-2-ones (having 3 to16 carbon atoms) with known logP values (determination of the logPvalues by the retention times using linear interpolation between twosuccessive alkanones).

The lambda-max values were determined in the maxima of thechromatographic signals using the UV spectra from 200 nm to 400 nm.

Starting Materials of the Formula (VI):

Example (VI-1)

2.8 g (11 mmol) of1-amino-4-cyano-2-fluoro-5-(4-methoxy-phenoxy)-benzene are initiallycharged in 100 ml of methylene chloride with 1.7 g of pyridine and, atroom temperature (approximately 20° C.), admixed with 1.25 g (12 mmol)of ethyl chloroformate. The mixture is stirred at room temperature for 2hours and then shaken with 1N hydrochloric acid. The organic phase isconcentrated under waterpump vacuum, the residue is crystallized withdiethyl ether/diisopropyl ether and the solid product is isolated byfiltration with suction.

This gives 1.2 g (34% of theory) of O-ethylN-(4-cyano-2-fluoro-5-(4-methoxy-phenoxy)-phenyl)-carbamate. ¹H-NMR(D6-DMSO, δ): 7.85 and 7.89 ppm.

Starting Materials of the Formula (IX):

Example (IX-1)

At room temperature, 1.3 g (10 mmol) of 4-methoxy-phenol in 100 ml ofN-methyl-pyrrolidone are admixed with 0.50 g of sodium hydride (60%pure) and, after brief stirring, with 1.5 g of4-cyano-2,5-difluoro-aniline. The reaction mixture is then stirred at100° C. for 20 hours. After cooling, the mixture is diluted with waterand then with 1N hydrochloric acid, and the mixture is stirred for twohours, after which the solid product is isolated by filtration withsuction and dried on clay.

This gives 1.9 g (73% of theory) of1-amino-4-cyano-2-fluoro-5-(4-methoxy-phenoxy)-benzene of melting point135° C.

Analogously to Example (IX-1) it is also possible to prepare, forexample, the compounds of the general formula (IX) listed in Table 2below.

TABLE 2 (IX)

Examples of the compounds of the formula (IX) Ex. No. Q R⁴ R⁵ X_(n)Physical data IX-2 O F CN (3-)OCH₃ m.p.: 94° C. IX-3 O F CN (2-)OCH₃IX-4 O F CN (4-)Cl IX-5 O F CN (3-)Cl IX-6 O F CN (2-)Cl IX-7 O F CN(4-)OH IX-8 O F CN (4-)

IX-9 O F CN — IX-10 O F CN (4-)F IX-11 O F CN (3-)F IX-12 O F CN (2-)FIX-13 O F CN (4-)Br IX-14 O H CN (4-)OH IX-15 O H CN (4-)OCH₃ IX-16 O HCN (4-)Cl IX-17 O H CN (4-)F IX-18 O F CF₃ — IX-19 O F CF₃ (4-)CH₃ IX-20O F CF₃ (4-)OCH₃ IX-21 S H CN — IX-22 S F CN — IX-23 S F CN (4-)Cl IX-24S F CN (4-)F IX-25 O F CF₃ (4-)CN

USE EXAMPLES Example A

Pre-emergence Test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours,the soil is sprayed with the preparation of active compound such thatthe particular amount of active compound desired is applied per unitarea. The concentration of the spray liquor is chosen so that theparticular amount of active compound desired is applied in 1000 litersof water per hectare.

After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control.

The figures denote:

0%=no effect (like untreated control)

100%=total destruction

In this test, for example, the compounds of Preparation Examples 4 and 6show strong activity against weeds.

Example B

Post-emergence Test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants of a height of 5-15 cm are sprayed with the preparation ofactive compound such that the particular amounts of active compound areapplied per unit area. The concentration of the spray liquor is chosenso that the particular amounts of active compound desired are applied in1000 l of water/ha.

After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control.

The figures denote:

0%=no effect (like untreated control)

100%=total destruction

In this test, for example, the compounds of preparation examples 4 and 6show strong activity against weeds.

What is claimed is:
 1. A phenyluracil of the Formula (I)

wherein n represents the numbers 0, 1 or 2, R¹ represents hydrogen,amino or optionally cyano-, carboxyl-, fluorine-, chlorine-,C₁-C₄-alkoxy- or C₁-C₄-alkoxy-carbonyl-substituted C₁-C₄-alkyl, R²represents carboxyl, cyano, carbamoyl, thiocarbamoyl or in each caseoptionally fluorine-substituted C₁-C₄-alkyl or C₁-C₄-alkoxy-carbonyl, Xrepresents C₁-C₄-alkoxy-, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl-,C₁-C₄-alkylsulphonyl-, C₁-C₄-alkyl-carbonyl-, C₁-C₄-alkoxy-carbonyl-,C₁-C₄-alkenyl-oxycarbonyl-, C₂-C₄-alkinyl-oxycarbonyl-,C₁-C₄-alkylamino-carbonyl-, di-(C₁-C₄-alkyl)-amino-carbonyl-,phenoxycarbonyl-, benzyloxycarbonyl-, phenylaminocarbonyl-substitutedalkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkylaminohaving in each case 1 to 6 carbon atoms, represents dialkylamino havingin each case 1 to 6 carbon atoms in the alkyl groups, representsC₁-C₄-alkoxy-substituted alkylcarbonyl, alkoxycarbonyl,alkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy oralkylaminocarbonyloxy having in each case 1 to 6 carbon atoms in thealkyl groups, represents dialkylaminocarbonyl or dialkylaminocarbonyloxyhaving in each case 1 to 6 carbon atoms in the alkyl groups, representsphenylcarbonyloxy, represents in each case optionally fluorine-,chlorine- or bromine-substituted alkylcarbonylamino,alkoxycarbonylamino, alkylsulphonylamino, or represents in each caseoptionally cyano-, carboxyl-, fluorine-, chlorine-, bromine- orC₁-C₄-alkoxy-carbonyl-substituted alkenyl, alkenyloxy,alkenyloxy-carbonyl, alkinyl, alkinyloxy or alkinyloxycarbonyl having ineach case up to 6 carbon atoms, where in the case that n is greater than1, X may be the same or different.
 2. A phenyluracil according to claim1, wherein n represents the numbers 1 or 2, R¹ represents hydrogen,amino or optionally cyano-, carboxyl-, fluorine-, chlorine-,C₁-C₄-alkoxy- or C₁-C₄-alkoxy-carbonyl-substituted C₁-C₄-alkyl, R²represents carboxyl, cyano, carbamoyl, thiocarbamoyl or in each caseoptionally fluorine-substituted C₁-C₄-alkyl or C₁-C₄-alkoxy-carbonyl,and X represents hydroxyl, mercapto, amino, nitro, cyano, carboxyl,carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine,represents in each case optionally hydroxyl-, cyano-, carboxyl-,carbamoyl-, fluorine-, chlorine-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-,C₁-C₄-alkylsulphinyl-, C₁-C₄-alkylsulphonyl-, C₁-C₄-alkyl-carbonyl-,C₁-C₄-alkoxy-carbonyl-, C₂-C₄-alkenyl-oxycarbonyl-,C₂-C₄-alkinyloxycarbonyl-, C₁-C₄-alkylamino-carbonyl-,di-(C₁-C₄-alkyl)-amino-carbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-,phenylamino-carbonyl-substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl or alkylamino having in each case 1 to 6carbon atoms, represents dialkylamino having in each case 1 to 6 carbonatoms in the alkyl groups, represents in each case optionally cyano-,fluorine-, chlorine-, bromine- or C₁-C₄-alkoxy-substitutedalkylcarbonyl, alkoxy-carbonyl, alkylaminocarbonyl, alkylcarbonyloxy,alkoxycarbonyloxy or alkylaminocarbonyloxy having in each case 1 to 6carbon atoms in the alkyl groups, represents dialkylaminocarbonyl ordialkylaminocarbonyloxy having in each case 1 to 6 carbon atoms in thealkyl groups, represents phenylcarbonyloxy, represents in each caseoptionally fluorine-, chlorine- or bromine-substitutedalkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, orrepresents in each case optionally cyano-, carboxyl-, fluorine-,chlorine-, bromine- or C₁-C₄-alkoxy-carbonyl-substituted alkenyl,alkenyloxy, alkenyloxy-carbonyl, alkinyl, alkinyloxy oralkinyloxycarbonyl having in each case up to 6 carbon atoms.
 3. Aphenyluracil according to claim 1, wherein n represents the number 1, R¹represents hydrogen, amino or methyl, R² represents carboxyl, cyano,carbamoyl, methoxycarbonyl or trifluoromethyl, and X representshydroxyl, mercapto, amino, nitro, cyano, carboxyl, carbamoyl,thiocarbamoyl, fluorine, chlorine, bromine, methyl, represents in eachcase optionally cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-,methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- ori-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-,ethylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-,methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxy-carbonyl-,allyloxy-carbonyl-, 1-buten-3-yloxycarbonyl-, 2-buten-4-yl-oxycarbonyl-,propargyloxycarbonyl-, 1-butin-3-yloxycarbonyl-,2-butin-4-yloxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n-or i-propylaminocarbonyl, dimethylaminocarbonyl-,diethylamino-carbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-,phenylamino-carbonyl- or benzylaminocarbonyl-substituted methyl, ethyl,n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl,methylamino, ethylamino, n- or i-propylamino, n-, i-, s- ort-butylamino, represents dimethylamino or diethylamino, represents ineach case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n-or i-propoxy-substituted acetyl, propionyl, n- or i-butyroyl,methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl,acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy,ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy,ethylaminocarbonyloxy, n- or 1-propyl-aminocarbonyloxy, n- ori-butylaminocarbonyloxy, represents dimethylaminocarbonyl,diethylaminocarbonyl, dimethylaminocarbonyloxy ordiethylaminocarbonyloxy, represents n- or i-butylcarbonyloxy, representsphenylcarbonyloxy, represents in each case optionally fluorine- orchlorine-substituted acetylamino, propionylamino, n- or i-butyroylamino,methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino,methylsulphonylamino, ethylsulphonylamino, n- or i-propylsulphonylamino,n-, i-, s- or t-butylsulphonylamino, or represents in each caseoptionally cyano-, carboxyl-, fluorine-, chlorine-, methoxycarbonyl- orethoxycarbonyl-substituted ethenyl, propenyl, propenyloxy,propenyloxycarbonyl, ethinyl, propinyl, propinyloxy orpropinyloxycarbonyl.
 4. A phenyluracil according to claim 1, wherein Xrepresents hydroxyl, mercapto, amino, represents in each case cyano-,carboxyl-, carbamoyl-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-,methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-,ethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, acetyl-, propionyl-,n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- ori-propoxy-carbonyl-, n-, i-, s- or t-butoxycarbonyl-, allyloxycarbonyl-,1-buten-3-yloxycarbonyl-, 2-buten-4-yloxy-carbonyl-,propargyloxycarbonyl-, 1-butin-3-yloxycarbonyl-,2-butin-4-yloxycarbonyl-, methylamino-carbonyl-, ethylaminocarbonyl-, n-or i-propylaminocarbonyl-, dimethylaminocarbonyl-,diethylaminocarbonyl-, phenoxycarbonyl-, benzyloxy-carbonyl-,phenylaminocarbonyl- or benzylaminocarbonyl-substituted methyl, methoxy,ethyl, n- or i-propyl, n-, i-, s- or t-butyl, ethoxy, n- or i-propoxy,methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonylor ethylsulphonyl, represents in each case optionally cyano-, carboxyl-,carbamoyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-,methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-,ethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, acetyl-, propionyl-,n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- ori-propoxy-carbonyl-, allyloxycarbonyl-, 1-buten-3-yloxycarbonyl-,2-buten-4-yl-oxycarbonyl-, propargyloxycarbonyl-,1-butin-3-yloxy-carbonyl-, 2-butin-4-yloxycarbonyl-,methylaminocarbonyl-, ethylamino-carbonyl-, n- ori-propylaminocarbonyl-, dimethylaminocarbonyl-, diethylaminocarbonyl-,phenoxycarbonyl-, benzyloxycarbonyl-, phenylaminocarbonyl- orbenzylaminocarbonyl-substituted n-, i-, s- or t-butoxy, n- ori-propylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s-or t-butylamino, represents dimethylamino or diethylamino, represents ineach case cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- ori-propoxy-substituted methoxycarbonyl or ethoxycarbonyl, represents ineach case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n-or i-propoxy-substituted acetyl, propionyl, n- or i-butyroyl, n- ori-propoxycarbonyl, methylaminocarbonyl, ethylamino-carbonyl, n- ori-propylaminocarbonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy,methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy,methylaminocarbonyloxy, ethylaminocarbonyloxy, n- ori-propylaminocarbonyloxy, n- or i-butylaminocarbonyloxy, representsdimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminocarbonyloxy ordiethylaminocarbonyloxy, represents n- or i-butylcarbonyloxy, representsphenylcarbonyloxy, represents in each case optionally fluorine- orchlorine-substituted acetylamino, propionylamino, n- or i-butyroylamino,methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino,methylsulphonylamino, ethylsulphonylamino, n- or i-propylsulphonylamino,n-, i-, s- or t-butylsulphonylamino, or represents in each caseoptionally cyano-, carboxyl-, fluorine-, chlorine-, methoxycarbonyl- orethoxycarbonyl-substituted ethenyl, propenyl, propenyloxy,propenyloxycarbonyl, ethinyl, propinyl, propinyloxy orpropinyloxycarbonyl.
 5. A phenyluracil according to claim 1, wherein Xrepresents in each case cyano-, carboxyl-, carbamoyl-, methoxy-,ethoxy-, n- or i-propoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- ori-propoxycarbonyl-, allyloxycarbonyl-, 1-buten-3-yloxycarbonyl-,2-buten-4-yloxycarbonyl-, propargyloxycarbonyl-,1-butin-3-yloxy-carbonyl-, 2-butin-4-yloxycarbonyl-,methylaminocarbonyl-, ethylamino-carbonyl-, n- or i-propylaminocarbonyl,dimethylaminocarbonyl-, diethylaminocarbonyl-, phenoxycarbonyl-,benzyloxycarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl- (andoptionally additionally fluorine- or chlorine-) substituted methyl,ethyl, n-propyl, n-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- ors-butoxy, represents acetyloxy, propionyloxy, n- or i-butyroyloxy,methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy,methylaminocarbonyloxy, ethylaminocarbonyloxy, n- ori-propylaminocarbonyloxy, dimethylaminocarbonyloxy,diethylaminocarbonyloxy or phenylcarbonyloxy, represents n- ori-butylcarbonyloxy, represents dimethylamino, n- ori-butylaminocarbonyloxy, or represents in each case cyano-, carboxyl-,methoxycarbonyl- or ethoxycarbonyl- (and optionally additionallyfluorine- or chlorine-) substituted ethenyl, propenyl, propenyloxy,ethinyl, propinyl or propinyloxy.
 6. A phenyluracil according to claim1, wherein n represents 1 or 2, R¹ represents hydrogen or methyl, R²represents trifluoromethyl, carbamoyl, carboxyl, methoxycarbonyl orcyano, and X represents hydroxyl, mercapto, amino, nitro, cyano,carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, orrepresents in each case optionally cyano-, carboxyl-, carbamoyl-,fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-,methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-,allyloxycarbonyl-, propargyloxycarbonyl-, 1-buten-3-yloxycarbonyl-,2-buten-4-yloxy-carbonyl-, propargyloxy-carbonyl-,1-butin-3-yloxycarbonyl-, 2-butin-4-yloxycarbonyl-,methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-,dimethylaminocarbonyl, diethylamino-carbonyl-, phenoxycarbonyl-,benzyloxycarbonyl-, phenylaminocarbonyl- orbenzylaminocarbonyl-substituted methyl, ethyl, methoxy, ethoxy,methylthio, ethylthio, methoxycarbonyl or ethoxycarbonyl, or representsmethoxycarbonyl- or ethoxycarbonyl-substituted ethenyl, or X representsin each case cyano-, carboxyl-, carbamoyl-, methoxy-, ethoxy-, n- ori-propoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-,allyloxycarbonyl-, 1-buten-3-yl-oxycarbonyl-, 2-buten-4-yloxycarbonyl-,propargyloxycarbonyl-, 1-butin-3-yloxy-carbonyl -,2-butin-4-yloxycarbonyl-, methylaminocarbonyl-, ethylamino-carbonyl-, n-or i-propylaminocarbonyl-, dimethylaminocarbonyl-,diethylaminocarbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-,phenylaminocarbonyl- or benzylaminocarbonyl- (and optionallyadditionally fluorine- or chlorine-) substituted methyl, ethyl,n-propyl, n-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy,represents acetyloxy, propionyloxy, n- or i-butyroyloxy,methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy,methylaminocarbonyloxy, ethylaminocarbonyloxy, n- ori-propylaminocarbonyloxy, dimethylaminocarbonyloxy,diethylaminocarbonyloxy or phenylcarbonyloxy, represents n- ori-butylcarbonyloxy, represents dimethylamino, n- ori-butylaminocarbonyloxy, or represents in each case cyano-, carboxyl-,methoxycarbonyl- or ethoxycarbonyl- (and optionally additionallyfluorine- or chlorine-) substituted ethenyl, propenyl, propenyloxy,ethinyl, propinyl or propinyloxy.
 7. A phenyluracil according to claim1, wherein n represents 1 or 2, R¹ represents methyl, R² representstrifluoromethyl, carbamoyl, carboxyl, cyano or methoxycarbonyl.
 8. Aphenyluracil according to claim 1, wherein n represents 1 or 2, R¹represents hydrogen, and R² represents trifluoromethyl, carbamoyl,carboxyl, cyano or methoxycarbonyl.
 9. A substituted phenyluracilaccording to claim 1, wherein n represents 1 or 2, R¹ representshydrogen or methyl, and R² represents trifluoromethyl.
 10. A compound ofthe Formula (IA)

wherein R¹ represents hydrogen or methyl, R² represents trifluoromethyl,and X represents in each case carboxyl-, methoxycarbonyl-,ethoxycarbonyl-, n- or i-propoxycarbonyl-, methylaminocarbonyl-,ethylaminocarbonyl-, dimethylaminocarbonyl-, diethylaminocarbonyl- orphenylaminocarbonyl-substituted methyl, ethyl, methoxy, ethoxy, or Xrepresents n- or i-butylaminocarbonyloxy, n- or i-butylcarbonyloxy,dimethylamino, methoxycarbonyloxy, ethoxycarbonyloxy,methylaminocarbonyloxy, ethylaminocarbonyloxy, or representsdimethylaminocarbonyloxy.
 11. A compound of the Formula (IA) accordingto claim 10, wherein R¹ represents hydrogen or methyl, R² representstrifluoromethyl, and X represents in each case carboxyl-,methoxycarbonyl- or ethoxy-carbonyl-substituted methyl, methoxy orethoxy, or X represents methoxycarbonyloxy, ethoxycarbonyloxy,methylaminocarbonyloxy or ethylaminocarbonyloxy.
 12. A compound of theFormula (IB)

wherein X¹ represents 4-(1-carboxy)-ethoxy, 4-(1-ethoxycarbonyl)-ethoxy,3-(1-ethoxycarbonyl)-ethoxy, 3-ethoxycarbonylmethoxy or2-(1-ethoxy-carbonyl)-ethoxy.
 13. A compound of the Formula (IB)according to claim 12, wherein X¹ represents 4-ethylaminocarbonyloxy,4-(n- or i-)butylaminocarbonyloxy, 3-methylaminocarbonyloxy or2-methylaminocarbonyloxy.
 14. A compound of the Formula (IB) accordingto claim 12, wherein X¹ represents 2-chloro, 3-chloro, 4-chloro,3-fluoro, 4-fluoro, 3-methyl, 3-cyano, 4-cyano, 2-methylthio,2-methylsulphinyl or 4-methylsulphinyl.
 15. A compound of the Formula(IC)

wherein X¹ represents dimethylaminocarbonylmethoxy ormethylaminocarbonylmethoxy and X² represents methyl.
 16. A compound ofthe Formula (IC) according to claim 15, wherein X¹ represents hydroxylor methoxy, and X² represents methyl.
 17. A compound of the Formula (ID)

wherein X¹ represents phenylaminocarbonylethoxy orphenylaminocarbonylmethoxy.
 18. A compound of the Formula (ID) accordingto claim 17, wherein X¹ represents n- or i-butylcarbonyloxy orethoxycarbonyloxy.
 19. A compound of the Formula (IE)

wherein X¹ represents dimethylamino and R¹ represents hydrogen ormethyl.
 20. A compound of the Formula (IF)

wherein X¹ represents 2-chloro, 3-chloro, 4-chloro, 2-fluoro, 4-fluoro,3-methyl, 3-nitro, 4-methyl, 3-cyano, 4-cyano, 2-methylthio, 4-nitro,2-cyano, 4-methylthio or 2-methoxy.
 21. A compound of the Formula (IG)

wherein X_(n) represents (3,4-)Cl₂ or (2,4-)F₂.
 22. A compound of theFormula (IH)

wherein X_(n) represents (3,4-)Cl₂ or (2,4-)F₂.
 23. A compound of theFormula (IJ)

wherein X¹ represents 4-methoxy, 3-chloro or 4-cyano.
 24. A compound ofthe Formula (IK)

wherein X¹ represents 3-trifluoromethyl, 4-chloro, 3-methoxy, 3-chloroor 4-cyano.
 25. A compound of the Formula (IL)

wherein X¹ represents 3-methoxy, 3-chloro or 4-cyano.
 26. A compound ofthe Formula (IM)

wherein X¹ represents 3-trifluoromethyl, 4-chloro, 3-methoxy, 3-chloroor 4-cyano.
 27. A compound of the Formula (IN)

wherein R² represents methoxycarbonyl, carbamoyl or cyano.
 28. Acompound of the Formula (IO)

wherein R² represents carbamoyl or cyano.
 29. An herbicidal compositioncomprising one or more substituted phenyluracil according to claim 1 andone or more extenders.
 30. A method for controlling undesirable plantscomprising the step of applying an effective amount of one or moresubstituted phenyluracils according to claim 1 to a member selected fromthe group consisting of said plant, a habitat of said plant andcombinations thereof.